This invention relates to certain herbicidal sulfonamides, agriculturally suitable compositions thereof and a method for their use as a general or selective preemergent or postemergent herbicide or as a plant growth regulant.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years which generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. No. 4,420,325 discloses, in part, herbicidal sulfonylureas of the formula ##STR1## wherein: R.sub.1 is F, Cl, Br, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkyl, NO.sub.2, CO.sub.2 R.sub.4, SO.sub.2 R.sub.5, SO.sub.2 NR.sub.6 R.sub.7, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 OCH.sub.2 CF.sub.3, OSO.sub.2 R.sub.5 or CH.sub.2 L;
L is SO.sub.2 NR.sub.6 R.sub.7, OCH.sub.3, OC.sub.2 H.sub.5, CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5 ; and PA1 R.sub.2 is H, Cl, Br, F, CF.sub.3 or OCH.sub.3. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl or C.sub.1 -C.sub.2 alkyl substituted by one of OCH.sub.3, SCH.sub.3 or CN; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.3 is C(O)(C.sub.1 -C.sub.3 alkyl), C(O)cyclopropyl, S(O).sub.2 (C.sub.1 -C.sub.3 alkyl) or C(O)phenyl; PA1 R.sub.4 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl or C.sub.1 -C.sub.2 alkyl substituted by one of OCH.sub.3, SCH.sub.3 or CN; PA1 R.sub.5 and R.sub.6 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.7 is H, CH.sub.3, CF.sub.3, F, Cl, Br, NO.sub.2, OCH.sub.3 or SCH.sub.3 ; PA1 R.sub.8 is H or CH.sub.3 ; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, CH.sub.2 OCH.sub.3 or Cl; PA1 Y is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, NHCH.sub.3 or N(CH.sub.3).sub.2 ; and PA1 Z is CH or N; PA1 a) when X is Cl, then Y is C.sub.1 -C.sub.2 alkoxy, and Z is CH; and PA1 b) when X is C.sub.1 haloalkoxy, then Z is CH. PA1 1. Compounds of Formula I wherein R.sub.9 is H; X is CH.sub.3 or OCH.sub.3 ;and Y is CH.sub.3 or OCH.sub.3. PA1 2. Compounds of Preferred 1 wherein R.sub.3 is C(O)CH.sub.3 or S(O).sub.2 CH.sub.3. PA1 3. Compounds of Preferred 2 wherein R.sub.1 is C.sub.1 -C.sub.3 alkyl; R.sub.4 is C.sub.1 -C.sub.3 alkyl; and R.sub.7 is H. PA1 2-[1-(Acetyloxy)ethyl]-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]benz enemethanesulfonamide (R is C(OR.sub.3)R.sub.2 R.sub.4, R.sub.2 is H, R.sub.3 is C(O)CH.sub.3, R.sub.4 is CH.sub.3, R.sub.7 and R.sub.8 are H, X and Y are OCH.sub.3, and Z is CH; m.p. 68.degree.-70.degree. C.) PA1 2-Acetyl-N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]carbonyl]benzenemethanesul fonamide (R is C(O)R.sub.1, R.sub.1 is CH.sub.3, R.sub.7 and R.sub.8 are H, X and Y are OCH.sub.3, and Z is CH; m.p. 160.degree.-163.degree. C.(d)) and PA1 N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]-2-(1-hydroxyethyl)benzene methanesulfonamide (R is C(OH)R.sub.1 R.sub.2, R.sub.1 is CH.sub.3, R.sub.2 is H, R.sub.7 and R.sub.8 are H, X and Y are OCH.sub.3, and Z is CH; m.p. 147.degree.-150.degree. C.(d)). PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl or C.sub.1 -C.sub.2 alkyl substituted by one of OCH.sub.3, SCH.sub.3 or CN; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.3 is C(O)(C.sub.1 -C.sub.3 alkyl); C(O)cyclopropyl, S(O).sub.2 (C.sub.1 -C.sub.3 alkyl) or C(O)phenyl; PA1 R.sub.4 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl or C.sub.1 -C.sub.2 alkyl substituted by one of OCH.sub.3, SCH.sub.3 or CN; PA1 R.sub.5 and R.sub.6 are independently C.sub.1 -C.sub.2 alkyl; and PA1 R.sub.7 is H, CH.sub.3, CF.sub.3, F, Cl, Br, NO.sub.2, OCH.sub.3 or SCH.sub.3.
There is no disclosure in this reference of the compounds of the instant invention.